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Cucurbit[7]uril Host-guest Complexes with Drug Molecules Containing Isoquinoline Groups
| Content Provider | Semantic Scholar |
|---|---|
| Author | Kwok, Julian |
| Copyright Year | 2011 |
| Abstract | This thesis describes the host-guest chemistry between cucurbit[7]uril (CB[7]) and various guests that contain isoquinoline groups, including tacrine, papaverine, Nmethyl papaverinium, N-methyl laudanosinium, 6,7-dimethoxy-1,2,3,4,tetrahydroisoquinoline, N, N-dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolinium, α,α'-bis(isoquinolinium)-p-xylene and a series of 1,n-bis(isoquinolinium) alkane dications (Isq(CH2)nIsq, where n = 2, 4-6, 8-10 and 12). The stoichiometries and strengths of the host-guest interactions were studied using UV-visible and H NMR spectroscopy and high-resolution electrospray ionization mass spectrometry. A focus of this thesis is an investigation of the effects of varying the chemical structure within a series of isoquinoline-based guest on the strength of the binding affinity and the position and orientation of the guests relative to the cavity of CB[7]. The H NMR spectra indicates that CB[7] prefers the saturated ring of tacrine as opposed to the aromatic ring, resulting in a binding constant of (2.7 ± 0.25) x 10 M. The N-methylations of papaverine and 6,7-dimethoxy-1,2,3,4,-tetrahydroisoquinoline increased their respective binding constants from those of the protonated forms and changed the nature of the interaction of the guest with CB[7]. With protonated papaverine, CB[7] has no preference as to whether it binds to the dimethoxy isoquinolinium ring or the dimethoxybenzyl ring, while CB[7] prefers to bind to the dimethoxyisoquinolinium ring of the N-methylpapaverinium cation. CB[7] binds over the aromatic rings of the protonated 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, however, with the N,N-dimethyl derivative, CB[7] encapsulates the tetraalkylammonium |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | https://qspace.library.queensu.ca/jspui/bitstream/handle/1974/6811/Kwok_Julian_K_20119_MSc.pdf?isAllowed=y&sequence=1 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
